2-Amino-6-methylpyridine → Ethyl 5-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1971624Notes

Reaction equation

HRID 1971624 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>O1CCCC1>[CH2:15]([O:14][C:12]([C:11]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]2[CH:10]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 66144Ethyl bromopyruvate

Product 1

HCID 821015Ethyl 5-methylimidazo[1,2-a]pyridine-2-carboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-6-methylpyridine (5 g, 0.05 mol) was dissolved in tetrahydrofuran (100 mL). Ethyl bromopyruvate (9 g, 0.05 mol) was added and the mixture was refluxed for 4 hours. The reaction was cooled and the solid that formed was filtered to give 6 grams of 5-methylimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester. Rf 0.45, 2% methanol/dichloromethane; MS m/z 205 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureThe reaction was cooled
  3. customthe solid that formed
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-14eb88f6eb2848cfa9cf9535acbe2970
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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